ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 15, Problem 15.52P
(a) Draw the products (including stereoisomers) formed when
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Which products are formed when hydrobromic
acid is added to (a) trans-2-hexene, (b) 2-methyl-
2-pentene, and (c) 4-methylcyclohexene, and
how many regioisomers can be formed in each
case?
What is the major organic product of the following reaction?
(a)
(b)
NaBH4
CH3CH₂OH
?
(c)
(d)
OH
4
But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour.
(a) But-2-enal exists as two stereoisomers.
Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal.
(b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde.
(ii) Explain why this test gives a different result with aldehydes than it does with keton
(c) But-2-enal also reacts with sodium borohydride, NaBH4.
(i) Identify the organic compound formed in this reaction.
(ii) State the type of chemical reaction occurring.
(d) Precautions must be taken to prevent but-2-enal catching fire.
Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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- Ocimene, a compound isolated from the herb basil, has three double bonds and the IUPAC name 3,7-dimethylocta- 1,3,6-triene.(a) Draw its structure.(b) Draw the structure of the compound formed if enoughHBr is added to react with all the double bonds inocimene.arrow_forwardDraw the structure of the following compounds which parent names have been traced to a common name; (a)5-methyl-4-nitroimidazole (b)2-chloro-4-methoxythiazole.arrow_forwardDraw the organic product(s) formed upon the addition of HBr to (a) 2-methyl-2-pentene, (b) trans-2-hexene, and (c) 4-methylcyclohexene. How many regioisomers can be formed in each case?arrow_forward
- Draw the product and indicate the stereochemistry when the given alcohol is treated with each reagent: (a) HBr; (b) PBr3; (c) HCI; (d) SOCI, and pyridine.arrow_forwardDraw the organic products formed when cyclopentene is treated withfollowing reagent. [1] LiAlH4; [2] H2Oarrow_forwardComparing Two Different Methods of Hydration of an Alkene Draw the product formed when CH3CH2CH2CH2CH=CH2 is treated with either (a) H2O, H2SO4; or (b) BH3 followed by H2O2, HO−.arrow_forward
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